25245-34-5

Basic information

• Product Name: 1-Bromo-2,5-dimethoxybenzene
• Synonyms: 1-BROMO-2,5-DIMETHOXYBENZENE;2-BROMOHYDROQUINONE DIMETHYL ETHER;2,5-DIMETHOXYBROMOBENZENE;2-Bromo-1,4-dimethoxybenzene;Benzene, 2-bromo-1,4-dimethoxy-;1-Bromo-2,5-dimethoxybenzene,98%;Bromohydroquinone dimethyl ether;1-BROMO-2,5-DIMETHOXYBENZENE 98%
• CAS NO: 25245-34-5
• Molecular Formula: C₈H₉BrO₂
• Molecular Weight: 217.06
• EINECS: 246-756-7
• Product Categories: Aromatic Hydrocarbons (substituted) & Derivatives;Benzene derivates;API intermediates;Ethers;Organic Building Blocks;Oxygen Compounds
• Mol File: 25245-34-5.mol
• Article Data: 51

Chemical Properties

• Boiling Point: 130-131 °C (10 mmHg)
• Flash Point: >110°C
• Appearance: Clear colorless to yellowish liquid
• Density: 1.445 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0119mmHg at 25°C
• Refractive Index: 1.569-1.571
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Water Solubility: Insoluble in water.
• BRN: 2441884
• CAS DataBase Reference: 1-Bromo-2,5-dimethoxybenzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Bromo-2,5-dimethoxybenzene(25245-34-5)
• EPA Substance Registry System: 1-Bromo-2,5-dimethoxybenzene(25245-34-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26
• WGK Germany: 3
• TSCA: Yes
• HazardClass: IRRITANT
• Hazardous Substances Data: 25245-34-5(Hazardous Substances Data)

Usage

Chemical Properties

clear colorless to yellowish liquid

Uses

Different sources of media describe the Uses of 25245-34-5 differently. You can refer to the following data:
1. 2-Bromo-1,4-dimethoxybenzene has been used in preparation of S-(-)-2-[N-(trifluoroacetyl)amino]-1-(2,5-dimethoxy-4- bromophenyl)-1-propanone, 1,4-bis{4-[2-(4-pyridyl)ethenyl]phenyl}butadiyne and 1,4-bis{2,5-dimethoxy-4-[2-(4-pyridyl)ethenyl]phenyl}butadiyne and 1-bromo-4-iodo-2,5-dimethoxybenzene. It can be used as a chemical redox shuttle additive in Lithium ion batteries for repeated overcharge and overdischarge protection.
2. 1-Bromo-2,5-dimethoxybenzene has been used in preparation of:S-(-)-2-[N-(trifluoroacetyl)amino]-1-(2,5-dimethoxy-4- bromophenyl)-1-propanone1,4-bis{4-[2-(4-pyridyl)ethenyl]phenyl}butadiyne and 1,4-bis{2,5-dimethoxy-4-[2-(4-pyridyl)ethenyl]phenyl}butadiyne1-bromo-4-iodo-2,5-dimethoxybenzene

InChI:InChI=1/C8H9BrO2/c1-10-6-3-4-8(11-2)7(9)5-6/h3-5H,1-2H3

Synthetic route

1,4-dimethoxybezene (150-78-7) → 1-bromo-2,5-dimethoxybenzene (25245-34-5)

Conditions	Yield
With (CH3)4Br In liquid sulphur dioxide at -23℃; Rate constant;	100%
With (CH3)4Br In liquid sulphur dioxide at -23℃;	100%
With Selectfluor; sodium bromide In acetonitrile at 20℃; for 113h;	100%

2-bromo-4-methoxyphenol (17332-11-5) + methyl iodide (74-88-4) → 1-bromo-2,5-dimethoxybenzene (25245-34-5)

Conditions	Yield
With potassium carbonate In acetone at 20℃; Inert atmosphere; Cooling with ice;	97.9%

2-bromo-4-methoxyphenol (17332-11-5) + dimethyl sulfate (77-78-1) → 1-bromo-2,5-dimethoxybenzene (25245-34-5)

Conditions	Yield
Stage #1: 2-bromo-4-methoxyphenol With potassium carbonate In acetone at 20℃; for 0.166667h; Stage #2: dimethyl sulfate In acetone at 20℃; for 12h;	97%

2-bromobenzene-1,4-diol (583-69-7) + methyl iodide (74-88-4) → 1-bromo-2,5-dimethoxybenzene (25245-34-5)

Conditions	Yield
With sodium hydride	83%

2,5-dimethoxyphenylboronic acid (107099-99-0) → 1-bromo-2,5-dimethoxybenzene (25245-34-5)

Conditions	Yield
With tetrabutylammomium bromide; copper(ll) bromide In water at 100℃; Sealed tube;	78%

potassium (2,5-dimethoxyphenyl)trifluoroborate → 1-bromo-2,5-dimethoxybenzene (25245-34-5)

Conditions	Yield
With tetra-N-butylammonium tribromide In tetrahydrofuran; water at 20℃; for 0.333333h; chemoselective reaction;	72%
With tetra-N-butylammonium tribromide In tetrahydrofuran; water at 20℃; for 0.333333h; chemoselective reaction;	72%

2-bromobenzene-1,4-diol (583-69-7) + dimethyl sulfate (77-78-1) → 1-bromo-2,5-dimethoxybenzene (25245-34-5)

Conditions	Yield
With alkali

1,4-dimethoxybezene (150-78-7) → 1,4-dibromo-2,5-dimethoxybenzene (2674-34-2) + 1-bromo-2,5-dimethoxybenzene (25245-34-5)

Conditions	Yield
With phosphorus pentabromide Erwaermen auf dem Dampfbad;
With hydrogenchloride; potassium nitrate; sodium bromide In diethyl ether; water at 25℃; for 4h; Time;

phosphorus pentabromide (7789-69-7) + 1,4-dimethoxybezene (150-78-7) → 1,4-dibromo-2,5-dimethoxybenzene (2674-34-2) + 1-bromo-2,5-dimethoxybenzene (25245-34-5)

4-methoxy-phenol (150-76-5) → 1-bromo-2,5-dimethoxybenzene (25245-34-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / acetonitrile / 3 h / 0 - 20 °C 2.1: potassium carbonate / acetone / 0.17 h / 20 °C 2.2: 12 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: bromine / dichloromethane / 2 h / Cooling with ice 2: potassium carbonate / acetone / 20 °C / Inert atmosphere; Cooling with ice View Scheme

hydroquinone (123-31-9) → 1-bromo-2,5-dimethoxybenzene (25245-34-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / acetone / 12 h / 20 °C 2: bromine; acetic acid / 1 h / 0 - 20 °C View Scheme

1-bromo-2,5-dimethoxybenzene (25245-34-5) + cyclohexane-1,2-epoxide (286-20-4) → C14H20O3 (500554-45-0)

Conditions	Yield
Stage #1: 1-bromo-2,5-dimethoxybenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: cyclohexane-1,2-epoxide With boron trifluoride diethyl etherate In tetrahydrofuran at -78℃;	100%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + 2-methyl-but-3-yn-2-ol (115-19-5) → 2-methyl-4-(2,5-dimethoxyphenyl)-3-butyn-2-ol (22944-10-1)

Conditions	Yield
With trisodium tris(3-sulfophenyl)phosphine; palladium diacetate; triethylamine In water; acetonitrile at 80℃; for 8h; Sonogashira Cross-Coupling;	99%
With piperidine; copper(l) iodide; triphenylphosphine; palladium dichloride at 80℃; for 12h; Sonogashira Cross-Coupling;	90%
With copper(l) iodide; triethylamine; triphenylphosphine; palladium diacetate at 80℃; Sonogashira coupling;	40%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 12h; Sonogashira cross-coupling;

2-[4,5-dihexyl(1,1'-biphenyl)-2-yl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1353713-99-1) + 1-bromo-2,5-dimethoxybenzene (25245-34-5) → 2,5-dimethoxy-4',5'-dihexyl-1,1':2',1''-terphenyl (1353714-02-9)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; palladium diacetate In water; toluene at 20 - 100℃; for 0.05h; Suzuki coupling;	99%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + (±)-2-methyl-but-3-yne-1,2-diol (21433-93-2) → 4-(2,5-dimethoxyphenyl)-2-methylbut-3-yne-1,2-diol

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); N-butylamine for 21h; Sonogashira Cross-Coupling; Inert atmosphere; Heating;	99%

dimethylmonochlorosilane (1066-35-9) + 1-bromo-2,5-dimethoxybenzene (25245-34-5) → (2,5-dimethoxyphenyl)dimethylsilane (1393446-11-1)

Conditions	Yield
With iodine; magnesium In tetrahydrofuran at 20℃; Inert atmosphere; Schlenk technique;	99%

1-bromo-2,5-dimethoxybenzene (25245-34-5) → 1-bromo-2,5-dimethoxy-4-nitrobenzene (98545-68-7)

Conditions	Yield
With nitric acid In acetic acid at 20℃; for 0.25h;	98%
With nitric acid; acetic acid for 0.5h;	92%
With cerium(IV) ammonium nitrate supported on silica In dichloromethane for 0.25h; Ambient temperature;	87%

1-bromo-2,5-dimethoxybenzene (25245-34-5) → 2,2',5,5'-tetramethoxybiphenyl (4555-64-0)

Conditions	Yield
With (i-Pent2(C6H3))2(C3H2N2))PdCl2((C5H4N)Cl); tert.-butyl lithium In toluene at 20℃; for 1h; Schlenk technique; Inert atmosphere;	98%
With bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; zinc In tetrahydrofuran at 50℃; for 20h; Inert atmosphere;	70%
With iron; sodium bromide; (2,2'-bipyridine)nickel(II) dibromide In methanol; ethanol Reduction; Electrolysis;	29%
With n-butyllithium; Trimethyl borate; sodium carbonate; tetrakis(triphenylphosphine) palladium(0) 1) THF, -78 deg C -> room temperature, 4 h; room temperature, overnight, 2) THF, EtOH, H2O, toluene, reflux, 24 h; Yield given. Multistep reaction;

1-bromo-2,5-dimethoxybenzene (25245-34-5) + phenylboronic acid (98-80-6) → 2,5-dimethoxy-1,1′-biphenyl (54113-30-3)

Conditions	Yield
With potassium fluoride; 2-(diphenylphosphino)phenylferrocene; tris-(dibenzylideneacetone)dipalladium(0) In tetrahydrofuran at 20℃; for 24h; Suzuki-Miyaura coupling;	98%
With dihydrogen dichloro-bis(di-tert-butylphosphinito-κP)palladium(2-); caesium carbonate In 1,4-dioxane at 100℃; for 20h; Suzuki-Miyaura cross-coupling reaction;	97%
With potassium carbonate In water; isopropyl alcohol at 60℃; for 4h; Catalytic behavior; Suzuki-Miyaura Coupling;	92%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + Lithium enolate of the acetaldehyde (675825-21-5) → 2,5-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-ol (87046-36-4)

Conditions	Yield
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran at -78℃; regioselective reaction;	98%
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere;	61%

trifluoroethylamine (753-90-2) + 1-bromo-2,5-dimethoxybenzene (25245-34-5) → C10H12F3NO2

Conditions	Yield
With bis(η3-allyl-μ-chloropalladium(II)); 5-(di(adamantan-1-yl)phosphino)-1′,3′,5′-triphenyl-1′H-1,4′-bipyrazole; potassium phenolate In 1,4-dioxane at 100℃; for 6h; Sealed tube; Inert atmosphere;	98%
With bis(η3-allyl-μ-chloropalladium(II)); 5-(di(adamantan-1-yl)phosphino)-1′,3′,5′-triphenyl-1′H-1,4′-bipyrazole; potassium phenolate In 1,4-dioxane at 100℃; for 6h; Sealed tube; Glovebox;	98%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + 1-t-Butoxycarbonylpiperazine (57260-71-6) → tert-butyl 4-(2,5-dimethoxyphenyl)piperazine-1-carboxylate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 16h; Inert atmosphere;	97.01%

(E)-1-octen-1-ylboronic acid (42599-16-6) + 1-bromo-2,5-dimethoxybenzene (25245-34-5) → (E)-1-(2,4-dimethoxyphenyl)octene

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate In tetrahydrofuran at 40℃; for 24h; Suzuki-Miyaura coupling;	97%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + 4-nitrophenylboronic acid (24067-17-2) → 2,5-dimethoxy-4'-nitro-1,1'-biphenyl (112148-15-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In ethanol; water; toluene at 80℃; for 8h; Suzuki Coupling; Inert atmosphere;	95.83%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + chloro-diphenylphosphine (1079-66-9) → (2,5-dimethoxyphenyl)diphenylphosphine oxide (72666-56-9)

Conditions	Yield
With sodium hydrogen sulfate; n-butyllithium; ammonium chloride; dihydrogen peroxide In tetrahydrofuran; methanol; hexane; dichloromethane	95.8%

1-bromo-2,5-dimethoxybenzene (25245-34-5) → 2,5-dimethoxyaniline (102-56-7)

Conditions	Yield
With bis(tri-ortho-tolylphosphine)palladium(0); (R)-(-)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyl-di-tert-butylphosphine; ammonia; sodium t-butanolate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	95%
With copper(I) oxide; sodium azide; L-proline In dimethyl sulfoxide at 100℃; for 6h; Inert atmosphere;	71%
With potassium amide In ammonia	62%
Stage #1: 1-bromo-2,5-dimethoxybenzene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: With C10H17NO In tetrahydrofuran; toluene at -45℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water; toluene Inert atmosphere;	58%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + 1β,2α-dimethyl-5α-(t-butyldimethylsilyloxy)-1,2,4aβ,5,6,7,8,8aα-octahydronaphthalene-1α-carboxaldehyde (93605-93-7, 93605-94-8, 107136-09-4, 107136-10-7, 107136-11-8, 107136-12-9, 108586-11-4) → trans-5α-(tert-butyldimethylsilyloxy)-1α-[(2,5-dimethoxyphenyl)-hydroxymethyl]-1,2,4a,5,6,7,8,8a-octahydro-1β,2α-dimethylnaphthalene

Conditions	Yield
Stage #1: 1-bromo-2,5-dimethoxybenzene With magnesium; ethylene dibromide In tetrahydrofuran; diethyl ether for 2.5h; Metallation; Heating; Stage #2: 1β,2α-dimethyl-5α-(t-butyldimethylsilyloxy)-1,2,4aβ,5,6,7,8,8aα-octahydronaphthalene-1α-carboxaldehyde In tetrahydrofuran; diethyl ether at 0℃; for 0.5h; Grignard reaction;	95%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + trimethylsilylacetylene (1066-54-2) → ((2,5-dimethoxyphenyl)ethynyl)trimethylsilane (531504-78-6)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diethylamine; triphenylphosphine In N,N-dimethyl-formamide at 120℃; for 0.5h; Sonogashira Cross-Coupling; Microwave irradiation; Inert atmosphere;	95%
With piperidine; copper(l) iodide; triphenylphosphine; palladium dichloride for 24h; Sonogashira coupling; Heating;	89%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + propargyl alcohol (107-19-7) → 3-(2,5-dimethoxyphenyl)-prop-2-yn-1-ol

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); N-butylamine for 21h; Sonogashira Cross-Coupling; Inert atmosphere; Heating;	95%
With copper(l) iodide; diisopropylamine; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride In N,N-dimethyl-formamide at 80℃; for 18h;	29%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + 2-methyl-1-buten-3-yne (78-80-8) → 1,4-dimethoxy-2-(3-methylbut-3-en-1-yn-1-yl)benzene (22944-05-4)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N-butylamine at 0 - 100℃; for 21h; Catalytic behavior; Temperature; Sonogashira Cross-Coupling; Inert atmosphere;	94%

dimethylmonochlorosilane (1066-35-9) + 1-bromo-2,5-dimethoxybenzene (25245-34-5) → 2-bromo-1,4-dimethoxy-3-(dimethylsilyl)benzene

Conditions	Yield
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; diethyl ether at -110 - -80℃; for 1h; Solvent; Temperature; Glovebox; Inert atmosphere;	94%
With 2,2,6,6-tetramethylpiperidinyl-lithium In tetrahydrofuran; diethyl ether at -110 - -80℃; Inert atmosphere;	94%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + allyl bromide (106-95-6) → 2-allyl-1,4-dimethoxybenzene (19754-22-4)

Conditions	Yield
With magnesium In diethyl ether at 0 - 20℃; for 2h; Grignard Reaction; Inert atmosphere;	93%
With n-butyllithium; copper (I) iodide Yield given. Multistep reaction;
Stage #1: 1-bromo-2,5-dimethoxybenzene With iodine; magnesium In tetrahydrofuran for 4h; Reflux; Inert atmosphere; Stage #2: allyl bromide With copper(I) bromide; lithium bromide In tetrahydrofuran at 20℃; Inert atmosphere;

1-bromo-2,5-dimethoxybenzene (25245-34-5) + isobutyl vinylacetate (24342-03-8) → (E)-isobutyl 4-(2,5-dimethoxyphenyl)but-3-enoate

Conditions	Yield
With bis(tri-t-butylphosphine)palladium(0); N-Methyldicyclohexylamine In toluene at 110℃; for 12h; Heck Reaction; Inert atmosphere;	93%

salicylonitrile (611-20-1) + 1-bromo-2,5-dimethoxybenzene (25245-34-5) → 3-(2,5-dimethoxyphenyl)benzo[d]isoxazole

Conditions	Yield
With magnesium; triphenylphosphine In tetrahydrofuran; toluene at 90℃; for 4h; Reagent/catalyst;	93%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + acetyl chloride (75-36-5) → 1-(4-bromo-2,5-dimethoxyphenyl)ethanone (90841-64-8)

Conditions	Yield
With aluminium trichloride In nitrobenzene for 2h; Ambient temperature;	92%

1-bromo-2,5-dimethoxybenzene (25245-34-5) + (R)-2-methyl-2-[2'-(phenylmethoxy)ethyl]oxirane (252651-57-3) → (S)-4-benzyloxy-1-(2',5'-dimethoxyphenyl)-2-methylbutan-2-ol (300661-18-1)

Conditions	Yield
Stage #1: 1-bromo-2,5-dimethoxybenzene With iodine; magnesium In tetrahydrofuran for 4h; Metallation; Heating; Stage #2: (R)-2-methyl-2-[2'-(phenylmethoxy)ethyl]oxirane With dilithium tetrachlorocuprate In tetrahydrofuran at -78 - -20℃; Ring cleavage; Grignard reaction;	92%

1-bromo-2,5-dimethoxybenzene (25245-34-5) → 4-bromo-1-(4-bromo-2,5-dimethoxyphenyl)-2,5-dimethoxybenzene (200943-34-6)

Conditions	Yield
With boron trifluoride diethyl etherate; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at -40℃; for 1.5h;	91%
With iron(III) chloride In dichloromethane	70%
With iron(III) chloride In dichloromethane	68%
With aluminium trichloride; iron(III) chloride 1.) nitromethane, 30 min, RT 2.) nitromethane, RT, 5 h; Yield given. Multistep reaction;
Multi-step reaction with 2 steps 1: bis(triphenylphosphine)nickel(II) chloride; tetraethylammonium iodide; zinc / tetrahydrofuran / 20 h / 50 °C / Inert atmosphere 2: N-Bromosuccinimide / dichloromethane / 10 h / Reflux View Scheme

1-bromo-2,5-dimethoxybenzene (25245-34-5) + (2R,4R,5R,6R)-4-acetyl-5-benzyloxy-2-phenyl-6-vinyl-[1,3]dioxane (205934-63-0) → (2R,4R,5R,6R)-5-benzyloxy-4-[(1R)-1-hydroxy-1-(2,5-dimethoxyphenyl)-ethyl]-2-phenyl-6-vinyl-[1,3]dioxane + (2R,4R,5R,6R)-5-benzyloxy-4-[(1S)-1-hydroxy-1-(2,5-dimethoxyphenyl)-ethyl]-2-phenyl-6-vinyl-[1,3]dioxane

Conditions	Yield
With n-butyllithium; cerium(III) chloride In tetrahydrofuran at -78℃; for 2h;	A 2% B 91%
With n-butyllithium In tetrahydrofuran at 0℃;	A 58% B 32%

Upstream product

• 123-31-9 hydroquinone 
• 107099-99-0 2,5-dimethoxyphenylboronic acid 
• 17332-11-5 2-bromo-4-methoxyphenol 
• 74-88-4 methyl iodide 
• 150-76-5 4-methoxy-phenol 
• 77-78-1 dimethyl sulfate 
• 583-69-7 2-bromobenzene-1,4-diol 
• 7789-69-7 phosphorus pentabromide 
• 150-78-7 1,4-dimethoxybezene 

Downstream Products

• 446831-24-9 1-bromo-4-chloromethyl-2,5-dimethoxy-benzene 
• 21193-37-3 2-[(2,5-dimethoxyphenyl)amino]benzoic acid 
• 875842-95-8 1,4-dimethoxy-2-(4-methoxy-phenoxy)-benzene 
• 144061-99-4 (1H-Benzoimidazol-2-yl)-(2,5-dimethoxy-phenyl)-acetonitrile 
• 95514-73-1 2-(1-cyanobutyl)-1,4-dimethoxybenzene 
• 116377-32-3 α-(3',4'-dimethoxyphenyl)-2,5-dimethoxyphenylacetonitrile 
• 95514-71-9 1,4-dimethoxy-2-(N,N-dipropylamino)benzene 
• 72667-90-4 dimethyl-1,4-dimethoxyphenylcarbinol 
• 72667-91-5 2-propenyl-1,4-dimethoxybenzene 
• 2785-98-0 2,5-dimethoxybenzoic acid 
• 98635-85-9 (2,5-dimethoxyphenyl)(phenyl)methanol 
• 81194-56-1 1-hydroxy-4,5,8-trimethoxynaphthalene 
• 198473-40-4 N-acetyl-N-(2,5-dimethoxyphenyl)-4-cyano-2,5-dimethylaniline 
• 199180-32-0 C₂₄H₃₆O₅ 

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A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.

Regioselective Oxybromination of Benzene and Its Derivatives by Bromide Anion with a Mononuclear Nonheme Mn(IV)-Oxo Complex

Oxybromination of aromatic compounds by high-valent metal-oxo intermediates has yet to be explored despite extensive studies on the oxybromination of aliphatic C-H bonds of hydrocarbons. Herein, we report the regioselective oxybromination of methoxy-substituted benzenes by a nonheme MnIV-oxo complex binding scandium ions, [(Bn-TPEN)MnIV(O)]2+-(Sc(OTf)3)2 (1), in the presence of tetrabutylammonium bromide. The regioselective oxybromination occurs at the carbon atom with the highest positive charge via electron transfer (ET) from the methoxy-substituted benzenes to 1. ET driving force dependence of the rate constants of ET from methoxy-substituted benzenes to 1 is well fitted in light of the Marcus theory of ET. Under photoirradiation, the oxybromination of benzene by 1 can be achieved via ET from benzene to the photoexcited state of 1, although no reaction occurs between benzene and the ground state of 1 in the dark. To the best of our knowledge, this is the first example of reporting the stoichiometric regioselective oxybromination of the benzene ring by a synthetic high-valent Mn(IV)-oxo complex and the catalytic regioselective oxybromination reaction with a Mn(II) complex and a terminal oxidant.